Colleen McCreary recently gave managers at Credit Karma a message that could seem more apt for rising sixth graders than personal finance executives.

“Back to school is coming,” McCreary, the company’s chief people officer, recalled telling managers. “We’re getting excited about all of these returning-in-the-fall type activities.”

The company has been trying to get employees back to the office regularly for more than a year. First, the vaccine rollout gave executives hope that the office would be full again. Then there was “Wine Down Wednesday” in the company’s Charlotte, North Carolina, location, and kombucha by the firepit in the Oakland, California, building. Now Credit Karma’s leaders are relying on a different incentive: Labor Day. The latest corporate magical thinking is that September will herald the grand refilling of cubicles around the country.

Each pandemic fall has brought with it employers’ hopes of a broad-scale return to the office. Last year’s plans were derailed by the delta variant. But this time, business leaders are adamant that they won’t change course. Seriously.

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“I don’t like to take attendance or babysit, but managers should know where their people are,” McCreary said, adding that since February employees have been asked to come in at least a few days a week, though the number is not specified and different teams set their own guidelines.

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It’s been more than two years since the rules of the working world snapped. On all sides of the debate over returning to the office, the stakes feel high as ever. More than one-third of U.S. workers who can do their jobs from home want to stay permanently remote, according to recent data from Gallup. Meanwhile, executives realize that if they don’t persuade their employees to come back now, with pandemic restrictions eased in most areas, the new norms of flexible work will be hard to unstick. So, some sense a standoff coming. Bosses say the office deadlines are real; workers are testing just how much they mean that.

“Many leaders have had decades of experience having all the answers,” said Sheela Subramanian, vice president of Future Forum, a Slack-backed research consortium. “That’s why you’re seeing a lot of these top-down mandates of ‘You will do this,’ and the inevitable resistance to that.”

“I have seen an increased resolve among executives to figure out what’s next,” she added.

It’s either the end of an era of mute button fails, hybrid hiccups and making it up as we go along — or the beginning of outright rebellion.

“I don’t think there will be a big grand return to office,” said Christine Ratcliff, who works in online education and lives in Littleton, Colorado. “It seems like a trickle.” Ratcliff switched jobs last year and applied only for roles that would let her stay fully remote. She considers herself a night owl and bristles at the thought of a position requiring her to be alert early in the day. She feels comfortable at the desk in her one-bedroom apartment, seated under a whiteboard on which she has scrawled affirmations like “routine, not schedule.”

“I could see one company being like, ‘OK, today is the day we’re doing it; if we lose people we lose people,’” Ratcliff continued. “But in the culture as a whole, it’s probably going to be a constant struggle.”

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Some major companies brought workers back to the office in recent months as the winter’s omicron wave ebbed, including American Express, Microsoft and Goldman Sachs. But during the summer, workers took long-delayed vacations or worked from home more often, making offices feel ghostly quiet. Earlier this year, office attendance on Fridays was at 30%, far lower than it was on Wednesdays at 46%, according to data from Kastle.

Stephanie Dukes, the director of engineering at Credit Karma, said when she came in on summer Fridays she sometimes sat in the office social hub, called “The Spot,” because the area by her desk was too empty.

People were working remotely about 35% of the time this spring, according to a national survey from Stanford and other institutions. That is more than employers had expected. The same survey found that companies had planned for their employees to be remote just 30% of the time by 2022.

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In general, it’s been a period of surprises for business leaders — who are sometimes realizing they don’t know where their employees are working, even if they know it isn’t the office.

“One organization I spoke to had employees update their mailing address because they were sending out sweatshirts,” said Steve Black, chief strategy officer at the HR technology company Topia. “They found people in random places around the globe.”

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“There’s been a little bit of ostrich burying its head in the sand, a bit of ‘We’re trying to keep people safe and do our best,’” he added. “We’re starting to see folks formalize their policies.”

A number of companies, including Apple, Capital One, Comcast and The New York Times, are setting fresh guidelines around returning to the office for September.

For many workers, a fresh push from bosses means new forms of pushback. Chris Campbell, who manages a team at an advertising agency in Minneapolis, has been required to go into the office one day a week since May. This summer, executives at his agency have been discussing ramping up the return to office to two days a week, while Campbell keeps emphasizing how much he has gained from the freedoms of remote work.

“You’re able to be so much more present with your child and your partner,” he said. “And your dog.” (His is named Frida, a German wirehaired pointer with bushy brows.)

Campbell has assured his own direct reports they shouldn’t feel pressured to commute in, and gave two permission to leave Minneapolis and go permanently remote. “People are going to resist it pretty heavily,” he said broadly of return-to-office plans. “But it’s a pretty uphill battle.”

At Credit Karma, which has more than 1,500 employees, company leaders have persistently faced resistance on returning to the office. During several full-staff video meetings in 2020, McCreary recalled, leaders spent nearly all their time fielding questions about remote work. Much of the opposition she heard came from workers who said they were productive at home, found it easier to have a personal life with remote work and saw some competitors take the leap to permanent flexibility. The company terminated two employees for working in locations where the business isn’t authorized to operate.

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“It’s always, ‘Google is doing XYZ,’ or ‘Facebook is doing XYZ,’ or ‘Small startup down the street is doing XYZ,’ why can’t we?” McCreary said. “We’re very clear this is the choice we’ve made, and if people want to make another choice, there are lots of opportunities for people from Credit Karma to go work somewhere else.” Some Credit Karma employees have embraced the company’s approach on returning to the office, which sets the expectation that they work in person but allows them to pick which days. Patrick Kennedy, 28, a growth technology manager, joined the firm in February after leaving his previous job at a cable company because he had to work in person on Mondays, Tuesdays and Wednesdays. He said he often couldn’t get an exemption to stay home when last-minute child care obligations arose, while at Credit Karma he has more flexibility.

Kennedy now goes into the office frequently because he feels energized by his morning routine of bopping desk to desk, trash-talking his office pingpong opponents and finding colleagues who share his “Stranger Things” obsession.

“I’ll get someone on my team, we’ll stop and see Scotty who hired me, we’ll take the elevator to the eighth floor to say hi, chitchat,” Kennedy said. “I’m eager to get to work just because when something happens, I have to inform them of my own personal life gossip.”

At many companies, including Credit Karma, leaders have felt a growing sense of urgency to make their work arrangements more concrete, given the logistical bumps in that hazy middle ground between fully remote and fully in-person work. A recent survey of human resources professionals showed that 39% had found an employee working in a location where their business didn’t have tax approval to operate.

Comcast and NBCUniversal are shifting into a newly detailed return-to-office plan in September, in which U.S. office-based employees are asked to be in person on Tuesdays, Wednesdays and Thursdays. Previously, management asked employees to be in the office several days a week but didn’t specify which days, and some were finding it challenging to see their teammates.

At Apple, some employees recently circulated a petition demanding the option to keep working remotely after Labor Day. “This uniform mandate from senior leadership does not consider the unique demands of each job role nor the diversity of individuals,” members of the group Apple Together wrote.

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Apple declined to comment on the petition.

Beyond the white-collar workforce, which is centered in larger cities where people have longer commutes, a lot of people are working in person. Data from the Bureau of Labor Statistics found that last month just 7% of Americans worked from home at some point because of COVID. Researchers point out, though, that this figure underestimates the extent of remote work. The survey asks people whether they are working from home because of COVID. But more and more people are working from home not because of COVID, but because of the way the pandemic reshaped the norms of work.

Zoe Sands, who works at a financial services firm in Denver doing internal audits, learned that management wanted her to start coming in once a week starting in May. Then she heard the company is hoping to build up to three days a week by later this year. She has decided that she would try to negotiate with her manager if she is asked to come in more than two days.

Sands feels most at ease when she can wake up at 7:15 a.m., drink a Yerba Mate and immediately start answering emails without devoting time to doing her hair and makeup. Going into the office means spending part of her morning rooting through her closet looking for an outfit that doesn’t make her feel self-conscious.

“One day I was really stressed out because I couldn’t find anything to wear,” she said. “I was like, that’s a really dumb way to call in and not go to the office, because I’m having a wardrobe malfunction.”

But the strain of trying to remake lives and routines is far from trivial. In conversations with more than three dozen people, it is clear that many can’t picture squeezing themselves back into office life with all its constraints, from the discomfort of blazers to the sting of a hallway slight. Others are increasingly desperate to return to the version of working life that existed before the pandemic and can’t imagine entirely letting go of their in-person relationships.

As summer fades, people are increasing attempts to articulate those workplace needs. Campbell, for example, said he has been raising concerns about returning to the office with his managers, emphasizing the prospect of the company losing out on talent because its competitors are embracing more flexibility.

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Campbell has listened to his colleagues who ask: With the business winning awards and growing its client pool, what’s the point in returning to old ways of working?

While he has made his own reservations clear, Campbell worries that company leaders have made up their minds.

“There’s some sort of cultural linkage to August and September being the time people want to go back,” he added. “It’s tied to that, ‘We’ll get through summer and then we have real work to do.’” With two years of return-to-office wrangling under their belts, some managers are feeling more confident about spelling out their expectations, both to their employees and to job applicants.

“I’ve had conversations with candidates where they’re very much like, ‘I would prefer to work remote.’ Then I have people at the opposite end of the spectrum,” said Dukes, 40, the director of engineering at Credit Karma.

“Sometimes there are situations where we’re not going to align with a candidate,” she added. “That happens.”